


Orders from Table 1

by UnboundedFandomShipper



Category: Supernatural
Genre: Alternate Universe, Alternate Universe - Human, BAMF Castiel (Supernatural), Barista Dean Winchester, Basically both Cafe and Mafia AU, Cafe AU, Castiel is Called Jimmy (Supernatural), Charlie Bradbury & Dean Winchester Friendship, Charlie Bradbury Ships Castiel/Dean Winchester, Dean Winchester is Protective of Sam Winchester, Destiel - Freeform, M/M, Mafia AU, Mafia Boss Castiel, Meg Masters Ships Castiel/Dean Winchester, Other Additional Tags to Be Added, Sam Winchester Ships Castiel/Dean Winchester, Tags May Change
Language: English
Status: In-Progress
Published: 2020-08-30
Updated: 2020-09-12
Packaged: 2021-03-06 17:41:14
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 13,519
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26192827
Author URL: https://archiveofourown.org/users/UnboundedFandomShipper/pseuds/UnboundedFandomShipper
Summary: Dean Winchester is working as a barista in one of the cafes downtown. He has been working there to save up for his student loans at the university, helping pay out his brother’s current school fees, along with their everyday expenses. Insert a strange person that came by at the cafe in Dean’s late night shift, bloody from a stab wound. It turns out that helping out the rude, good-looking, blue-eyed stranger was one of the many decisions that he will be glad to take and live to regret, both at the same time. He says his name was James. Why does that name sound familiar?
Relationships: Castiel/Dean Winchester
Comments: 19
Kudos: 55





	1. Chapter 1

**Author's Note:**

> We'll see if I can commit to an everyday update. Enjoy reading and tell me what you think :D

_ Boring. boring and even more boring.  _ Serving coffee and tea and hot or cold beverages wasn’t something that Dean thought he would do. He could probably look for another job in another part of the city. Maybe he can ask for friends for help in seeking a different employment. He knew he could fix cars as a mechanic somewhere but he really didn't know if he could be employed. He knew that the pay here isn’t that good, but it isn’t as bad either.

He had to save up money to pay up for his student loan. He had to help his brother with his fees too. Law school is really an expensive career choice but Dean is more than willing to help out whatever makes Sam happy.

They both became orphans when Dean was four and Sam was a baby. Their house was caught in a house fire and both the boys were the only survivors. Unfortunately for them, life has never been easy. They were both taken in by the family friend, Robert Singer, who treated them like his own kids. Dean and Sam both owed him a lot so Dean promised Bobby that he didn’t have to pay for their college fees. The older Winchester promised he will handle all their expenses. Their guardian had refused before but after a little convincing, Dean took a student loan for his own degree and he is taking care of Sam’s school expenses too, apart from their everyday expenses.

Dean likes to think that after he graduates, it would be best to look for a job immediately so he can finally support Sam full-time. His brother was nearing college, after all. Sam had also mentioned that he wanted to apply for a scholarship, to lessen Dean’s burden. But he didn’t want to give his brother any pressure. If he were to be completely honest, he didn’t mind it one bit. He is willing to sacrifice everything, if it means that Sam will be happy.

It is currently his night shift at the Cafe Bonheur. He usually takes this schedule because he usually has classes in the morning. The owner, Mrs. Pamela, is the kindest person that Dean has ever met, apart from Bobby. She agreed to hire him despite his troublesome background and Dean is more than thankful. Sure, he is not the employee of the month, but he didn’t get into any troubles, like he did when he was younger. He wanted to prove that he and his brother can live a better life without Dean being the old troublemaker that he was. So far, it is working nicely.

Since their store is scheduled to be open 24/7, Dean has to be on his shift from 6pm-12am before he gets to leave. It’s still around 11pm, just an hour more and he can finally head home and sleep. He can vaguely remember that he had assignments to pass tomorrow. He hopes he can do those once he gets home, or when he wakes up in the morning. He barely has time to do both study and work but he has to.

He was humming a tune to himself as he started to clean some of the utensils that he had used. Everyone there appreciates it when the place is clean. He didn’t turn away from washing the blender when he heard the unmistakable sound of the ding when the door opened. He had to wait to be called after all.

“Do… Do you have any coffee recommendations?” The stranger’s voice was soft and slightly monotonous, Dean almost thought that he had imagined it.

The moment Dean turned around to answer, his eyes widened when he saw that the stranger was bleeding from his left side. He washed his hand and was immediately out of his counter to help out. “What the hell’s wrong with you man? You’re bleeding!”

“No kidding. You…You didn’t even answer my question.” The stranger had the audacity to use a rude tone. Dean felt his right eye twitch in slight irritation. He can hear the strain in his voice though and he can’t help but feel bad.

Dean helped him to sit down on the nearby chair. “Yeah sure. Let me go get the first aid. Stay there yeah? One sec.”

He knew that violence is more frequent outside, especially at a time like this. If this stranger managed to get away from a possible gang fight outside, it is all the more reason for Dean to help him out.

Dean returned from the employee’s only room with the box of first aid at hand. He stood beside the wounded stranger and removed his hand. “Here, let me see.” He slightly winced when he saw how bad it was. He took a chair and sat on it to start with cleaning. The stab wound was only shallow, but the bleeding was bad. He immediately set to work. It was nice that he was able to know how to dress wounds with bandages from how often Sam does it to him when he comes from a fight.

There were no exchanges of words between them. Dean was slightly feeling awkward because he can feel that he is being stared at. He can even hear the ticking of the hands from his watch.

When he was done, he hummed to himself. “There we go.” He says, more to himself. He looked up to meet the stranger’s stare. Bright blue eyes and unwavering stare, but it looks more like confusion to Dean than anything. “So, were you about to order something or you need to stay here for a bit? I can call 911 for you if you want that.” Dean offered.

“Coffee recommendation.” The stranger said, tilting his head to the side, just a hint.

Dean raised an eyebrow at him. “Huh right. Cold coffee shake thing, we have the best seller: Java chip. Hot coffee is uhh- Cafe au Lait.” He briefly turned to the counter to make sure. “But those with the marks at the menu are some of our best selling ones.”

“No, I mean your own coffee preference.”

Dean definitely doesn’t have enough energy for this. He wanted to argue but he stopped himself. Besides, the stranger was wounded and he had just covered up the wound. “Okay, uhh- I guess, Vietnamese Iced Coffee. But it’s cold out so you probably want something hot that would-”

“Get me that. Before your shift ends.” Was all he said.

They didn’t have any more interactions other than that. Dean finished making the order and the stranger, who said that his name was James, left without even a word of thanks. He did pay and gave him a generous tip, which threw Dean into a stunned silence. The moment the door closed, Dean was startled when he heard the alarm go off from the clock by the counter. It was midnight and finally the end of his shift. 

He left when his co-worker arrived to start her own shift. He wonders how the stranger knows his schedule, and why he was wounded in the first place.  
  


**_TBC_ **


	2. Chapter 2

**Summary for the Chapter:**

> Sam mentioned about his how he had gotten his scholarship. Why does Dean feel like he had heard Novak from somewhere? Just who is he?

**Notes for the Chapter:**

> I actually have this chapter in progress right after I posted yesterday's chapter. I was bored so yeee- But I do have classes currently and it's not fun because I have to stop typing. Then again, no one said schoolwork was fun ^^" Anyways, enjoy! :D

The next morning, Dean woke up from the sound of his alarm clock. He turned to face his brother’s bed a few feet away from his. Empty. It looks like Sam woke up earlier than he did. Again.

He groans and shifts on the bed, rolling over to plant his face on his pillow. He wakes up slow, and he intends to lay there until his alarm goes off again and he is more awake. He would definitely need that cup of coffee.  _ Nope,  _ he knew he was going to need two to survive the group meeting he had to be in. Besides, he can always drink more coffee back at his work when it wasn’t his shift yet. If he sees the owner and his employer, he knew that he’d probably get a freebie for the day. That was how kind Pamela is to her employees.

It took fifteen minutes before Dean heard the alarm go off again and this time, Dean was ready to get up. Turning off the alarm, he sat at the bed and stretched his arms. He can smell the unmistakable smell of pancakes in the air. It was a delight, since they rarely have them for breakfast. Even if Dean would always leave earlier than Sam, the younger would always wake up way earlier than the older. Usually, Dean would wake up with breakfast prepared.

He would tell his brother to let breakfast be prepared by him but Sam always insisted. Dean was easy to agree, but only because Sam would never forget to have coffee prepared for him too.

“Morning.” Dean greeted once he entered the kitchen. He covered his mouth as he yawned.

Sam looked at him, right after he placed one more pancake from the three-stack-pile of them on one plate. “Yeah, morning Dean. Here’s yours.”

Dean took a mug from their cupboard and poured himself the brewed coffee from the coffee maker. He blinked his eyes, no doubt making sure that he is really more awake for the day. “Thanks.”

“By the way,” Sam started, sitting on the chair. He was beginning to eat his own stack. He didn’t have anything with it other than butter. But Dean saw that they do have syrup in front of him. “Remember when I told you I applied for a scholarship?”

“Mhm. What about it?” Dean asked, walking over to the table. He took a sip of coffee, feeling the warmth envelope him.  _ Ah,  _ coffee is definitely life. 

“Yeah, well. Stanford wasn’t accepting a scholarship application when I applied so that’s disappointing. They said that my grades were great, but they also said that their slots were full.”

Stanford was Sam’s dream school and Dean was full of support for his decision. He didn’t hear any note of disappointment on Sam’s voice though, so Dean raised an eyebrow at him.

“Does that mean you’re gonna try out a different school for a scholarship? I mean I can always support your expenses at Stanford if that’s the school you really want.” He says. He finally started digging in. The pancakes were soft and fluffy. Definitely the best right after he poured a generous amount of syrup and a bit of butter on top.

Sam was looking at him with slight disgust, but Dean didn’t care. Sweetly-sweet was his type of pancake. “No, actually. They aren’t accepting scholarships anymore but they had someone come take an interest in my grades.”

“Soooo-?”

“So, I now have a sponsor. As long as I keep up with the maintaining grade, the sponsor will pay up for my education. Dean, I’m going to Stanford!” Sam is grinning.

Dean almost choke on his pancakes at the news. It was perfect! He drank from his mug and stood up to come hug his younger brother. “Hell yes! Man, I’m proud of you! I know you can make it!” He pulled back a bit before ruffling Sam’s long, wavy locks. 

Sam didn’t complain once at the treatment, which he would usually do. Instead, he was laughing along with his older brother. “You sound like an old man.” He says, closing one eye as he let his brother mess up his hair. He did feel disheartened when he heard the news about the unacceptance of application. He was really lucky that a sponsor is looking for someone they can support when he came for the call. They took interest in him! 

The sponsor was more than interested in granting him the opportunity and the younger Winchester is more than happy to, at least, lessen the pressure on the older. He didn’t want to be a burden on Dean, so he had been doing his best. Now, it looks like his efforts had paid off. And seeing how happy Dean is for him, it made Sam feel proud of his achievement.

“Do I get to meet the sponsor? I gotta thank them properly, man. Or is it a secret?” Dean paused, finally letting his brother go from the hug.

Sam nodded his head slightly. “Yeah, actually, the sponsor wanted to meet my guardian. Bobby’s a long drive away so you have to come. All he said was his name was Mr. Novak. He didn’t really give much details.”

Dean hums, returning back to his seat. “Good. Did they pick the place to meet up?”

“Yeah they did. They wanted to meet at the cafe you're working at. Apparently, they have a busy morning so they’re gonna meet up at around 7. Is that okay? You work the night shift there right?” Sam took a sip from his mug as he waited for Dean to reply. It was not the best time to pick for his brother. He knew how he barely has time in between going to uni and his job. But he also knew that Dean would like to meet the sponsor in person so Sam took the liberty to agree for him.

Dean nodded. “Well yeah. But Pamela has the new part-time recruit Aaron to come by so she can teach him the ropes. He’s gonna take the shift before me after Camille left. She said I can take the shift off for now. But yeah, ‘m supposed to work. You know I don’t really take breaks. Figured this is gonna be an exemption.” He took more from his pancakes. When he was halfway, he shook his head slightly. “Right. So what do they look like? Anything that makes them stand out or something?”

Sam placed his fork back on his empty plate, finishing his breakfast. He thought for a bit. He stood up and placed his plate on the sink. “He looks pretty average. Huh. Actually, I think the one I met is his assistant or something. Even asked for how you look. So, I did show him your pic so he said he’s going to come.” 

He was just about to ask about the assistant until Sam mentioned about the picture. Dread can be seen on his face, if the amused stare of Sam at his direction is anything to come by. “What? Which pic are we talking about?” Dean knew Sam had plenty of blackmail pic material of him and he didn’t want to hear any shit.

Sam was starting to laugh but he cleared his throat. “Just your face. Don’t worry, I didn’t show him the one where you’re wearing the pink boxer thing.”

“What the hell, Sammy!”

Needless to say, their morning became a chase of cat and mouse, until Dean had to prepare and leave for school. Still, the thought of the sponsor,  _ Mr. Novak  _ didn’t leave him the entire morning. Why was it so familiar?

-/-/-/-

Usually, Dean would be pulled aside by a senior or just about everybody who wants to pick up a fight with him. It would always happen on a Tuesday, which is the same day as today. The other days are unpredictable, but it always happens on one day so he is always ready.

Imagine his surprise when he was able to get through the day without one bully, senior or whoever was trying to get a rise from him. It was weird.

He wasn’t really complaining. He was able to come to all of his classes without supporting any kind of pain from punches to the side, or a black-eye even. Dean tried his luck and went by the library, because he needed to borrow a book to finish his project. He did see the jerk Brad, along with his lackeys. They only looked at him and left. What the hell?

When lunchtime came, Dean ate in the cafeteria. He was able to buy a meal that suits his tastes and appetite. Food outside was expensive and the only luxury of a cheap, greasy meal that Dean prefers, over Sam’s gross greens he calls salads, he can find it here no problem.

“What’s up bitches?”

Dean felt a hand on his shoulder and he turned to look. Charlie has her hand raised almost near his face, her fingers forming a ‘v’. It was her usual greeting and Dean gestured at his right to let his best friend sit.

“Yeah, Charlie. How’s it going?”

Charlie raised an eyebrow at him. “Woah, okay. Brad and his crap group of bad guys didn’t even try to corner me or something to ask for you. What did you do to make them cower like dogs with their tails between their legs?” She asks. She took her sandwich from her bag and began to nibble. “I swear, they looked horrified when they saw me. Damn- So yeah! Any tea to spill?”

“‘Bout that? I have no idea.” Dean answered, eating some of his fries before placing the container between them. They have the habit to share food after all. “Remember Irving? Used to give me the black eye before Chem right? Nothing. ‘S like they’re avoiding me. I saw Brad and his shitty group too and they didn’t even care.” He raised both hands in surrender for a bit before taking another bite from his hamburger. “I’m not complaining but if it’s just not me, guess they probably have a change of heart.”

“Pffft- change of heart. More like they probably have someone blackmail them or something. I mean you know how they usually leave me alone ‘cuz I got dirt on them. But if it’s not you then who?” Charlie took a bit of fries from Dean and hums. “I got Physics at 3 and library duty by 5. Guess we can’t hang out and play some games huh?” She says, sighing. “Man! And here I was wanting to beat your ass on it.”

Dean chuckled. “I barely have free time with a job, you reckless shit.” He raised his hand at him, which was greasy. He heard her gasp in alarm. So he scares her a bit by waving his hand near her face. “Yeah princess, get scared.” He was laughing until she smacked his shoulder.

“Jerk.” Charlie was also laughing beside him. Once she was done, she sighed, shaking her head slightly in amusement. “Honestly though, you might want to figure out why. Tell me when you know. I’d see if I can catch a whiff on why too. But yeah, Tuesday had never been this good for years man.”

Dean definitely agrees.

-/-/-/-

Pamela told him over the phone that he is free to come by for his freebie coffee and he cannot wait. Of course, he didn’t forget about meeting up with the sponsor who only mentioned his last name and had his secretary, assistant or whatever to meet up with Sam. Whoever it was, Dean is more than thankful that they are willing to support his brother in his studies. But even he can’t help but feel suspicious.

He took a short trip back home first so he can freshen up. Once he arrived, he noticed that Sam wasn’t home yet. He was probably over at Jessica’s for a group study. Dean knew that his brother definitely has the hots for her, but he didn’t know if his brother will actually make a move or let it be for a while. It was his brother’s business but Jessica obviously liked him back. They were looking at each other like honey and Dean is definitely rolling with ants around whenever he sees them together.

After the short stop, Dean is back on the streets again. It was a freezing cold night that he can’t help but remember the stranger from last night. He took Dean’s preferred, cold drink and left. He was also still wounded and the worry is there again. He should’ve called 911 on that person. Wherever he is, Dean hoped he had gotten medical attention if he needed that.

Since Cafe Bonheur is walking distance from the place he and Sam are living in, it took Dean no time to reach it. He opened the door, signalling the small bell sound that caught Pamella’s and the petite guy standing beside her, no doubt Aaron, attention. He approached them and Pamella gave him her usual hug greeting.

“Ah, you freezing cold boy! Did something happen? You rarely take a day off even if I offer them.” She says, pulling back a bit to make eye-contact with Dean.

Dean shrugged. “About that. Sam had gotten a scholarship from a sponsor and I have to meet him here so I had to. I’ll take overtime tomorrow.” He promised but Pamella merely pat his shoulder.

“Sheesh, take a break when you are given a break. Tell Sammy my congratulations and you-” She pinched his cheeks and Dean wanted nothing more than to leave already. His cheeks feel like it’s burning. “-I’m proud of you both. I’m gonna be showing Aaron here how to manage without Camille, for now. I did explain it in the text right? We’re here for your shift today. Off you go! Sit wherever. I’ll call you when I have your Vietnamese Iced Coffee freebie prepared, yeah?”

Dean nodded his head. He rubbed his burning cheeks as he sat at the chair at the far-right. His position allowed him to see who was coming in from the door and who is leaving. He wanted to see who Sam’s sponsor was for longer before recognition settled in. He is someone that Dean is thankful for. He can’t wait to meet him, whoever he is.

It was a half an hour before 7pm and Dean was already getting bored as he waited. Since his drink is a freebie, it wasn’t a priority so he still doesn’t have it. There are a lot of people, like it usually is at the current time. People usually start to leave when it starts ticking to 10 and by 11, the cafe is usually quiet with a few, occasional patrons that would take to-go orders. Dean was now scrolling through his phone when he felt someone stand in front of him. He looked at the table in front of him when he heard a small thud. Atop it has two orders of Vietnamese Iced Coffee, his favorite.

Dean was just about to tell whoever this is that he only had one order when he noticed the stranger was wearing a suit and a trenchcoat. This wasn’t Aaron. He looked up and his eyes widened when they made eye contact with an unwavering stare from blue eyes. He is the very same person from last night. “What… What are you doing here man? You were bleeding. Did you get that sorted better?” Ah shit- he was rambling. But he is worried. Dean knew that he could dress the wound but there could be times he does it with a shitty quality.

Well  _ shit. _

A tilt of the head to the side, before the stranger took the seat right in front of him. He offered his hand. He even ignored all the rambling Dean had said earlier. “Dean Winchester, right?” He asked.

Dean could only nod in surprise.

The stranger smiled. “I’m James Novak. I am Sam’s sponsor. Pleasure to meet you.”

_ James Novak.  _ Why is that name familiar? Why does it feel like Dean knows it from somewhere?

Dean only stared at him, unmoving for a bit. James Novak was a name that he knew from before. It felt like it was a secret. His head is starting to feel like it was pounding as he tried to remember why the name makes the hair on his skin rise in slight anticipation?

Only one word came to mind… But it wasn’t only a word, it was a name.

“...Castiel?”

**_TBC_ **


	3. Chapter 3

**Summary for the Chapter:**

> Dean has a pounding headache. Apparently, it is a side-effect of remembering something from the past.

**Notes for the Chapter:**

> Henwo! Forgive my lazy and forgetful ass. I forgot to update yesterday. Anyway, here's the update for today. I also have a word limit for myself that I can't follow so every chapters' end might sound/look shitty.

Dean slowly blinked his eyes. It was still dark, but only because he felt a fabric covering his eyes. Alarm and adrenaline flowed in his veins when he realized that he was bound to a chair with a blindfold on. He struggled from the binds, trying to see if he can get out using sheer force. What the hell is going on?

He breathed in from his nose and out his mouth, trying to calm down the panic. He had to be calm enough so he could guarantee his own safety. His head is still pounding from a bad headache. He figured it was from last night, but the ache also felt as if he was hit with a blunt object enough to knock him out.

He tried to remember what happened between the meeting to his current predicament. 

/-/-/-/

**_Flashback_ **

It would seem like  _ James Novak  _ has no idea how to mask his expression like how he puts himself up to be because Dean can see the surprise as clear as day on the other’s face. He raised an eyebrow at him and it took a bit of time for James to recover.

James cleared his throat and took a sip from his drink. Anyone with eyes can see that he is now nervous. “Excuse me, who?”

Dean looked at him with an unamused stare. “James- I can call you James right? Anyway,  _ James. _ ” He emphasized, looking around them. No one’s paying attention but it is a pretty crowded place. He didn’t want to make a scene at the very same cafe that he is working in. “I don’t know why I said that word the moment I saw your face and heard you say your name. But I’m not stupid to see that you’re lying when you say you don’t recognize whatever name I said.”

This time, James was able to keep up the neutral expression, even if his eyes tell a different story. Those blue eyes that Dean had never forgotten since yesterday was now filled with worry. Worry for what, he didn’t know. 

“ _ Dean. _ ” James started, a small sigh escaping his lips. “That’s not… that’s not a name you should say out here in public. Too crowded and noisy. Besides, headaches are pretty common for memories that might come with when remembering something from the pas-”

“Woah, woah, woah. Hang on-” almost choking from the drink he had decided to sip at the moment, Dean cleared his throat. He was not expecting a straightforward answer. He thought that the earlier slip in expression and the denial would mean even more denial. No, it would seem that he is more blunt than he thought. “So, hang on man. Are you saying we met in the past and no offense but I’m getting confused man.”

James nodded his head. “Yes. But it is not of import that I like to talk about now. I wanted to meet you about the sponsorship for Sam, not this.”

“Sure.” Dean agrees. James has offered to pay for his brother’s educational expenses and whatever this thing is, Dean is not about to make a big deal out of it, at least, not yet. Sure, he is inwardly freaking out, but they meet up with Sam’s education in their mind. He knew they will have the time to talk about this in the future, so he’s going to let it slide for now. “So how does the sponsor thing work?”

“Right. All I can tell you is your brother would be able to continue his education as long as he can keep up with the maintaining grade. I’m sure he won’t have any problems with that.” James started. He was looking at Dean with seriousness, his stance was all business-like. 

“Damn right, he won’t.”

“Good. One failed subject cuts his scholarship off and we don’t want that.” James added. “Yes, I know, I specifically made sure that when I heard a ‘Sam Winchester’ applying for a university currently full of scholars that I would sponsor him there. I owe you at least that.” 

“Okay, so let me get this straight.” Dean placed his right hand on the table, took his drink with his left and sipped from the straw before placing it back down. “So, the scholarship thing is granted for Sammy just because you actually owe me? Man, did I save your life back then or something?”

James nodded. “More so than you thought.”

“Sure, let’s go with that. But how do I know there’s no strings attached?” Dean knew he had every right to be suspicious. Sam’s education is at stake here and he didn’t want it to be used just for some kind of hidden agenda. He wanted his brother to be happy and he is going to do whatever it takes for him to be. “You came here to talk to me, triggered a memory or something I had or crap, and now you say you are giving a scholarship to Sammy because you owe me. What’s it to you, man? No offense, but you’re even more suspicious because of what happened last night.”

Patience is wearing thin on James’ end. It’s not like Dean can see it yet, but he will soon enough. “None taken. And I know you have the right to be skeptical. My first impression from last night didn’t help.”

“No shit Sherlock.”

James cleared his throat at the interruption. “But if you would give it a chance, I am not bounding your brother with strings or some equivalent of it. That was me repaying what I owe you in the past, even if you don’t remember it. If you allow me to, I would like to offer help in paying out your student loans in the future too.”

“Pump the breaks, man.” Dean is getting tired of this bullshit. He closed his eyes and massaged his own forehead with his pointer finger and thumb. The headache is getting worse now. “Hang on. Why are you doing this?” He stares right at the other’s eyes in irritation. “And don’t give me the crap that you owe me because I don’t remember it so you don’t.”

“I never break promises,  _ Dean _ .” James sighed. He leans back on his chair, clearly feeling even more tired than he was earlier. “Remember it or not, I intend to keep my word. We can talk more about the latter subject in the future. Rest assured your brother’s scholarship is and never will be manipulated.” He took a piece of paper from the inner pocket of his trenchcoat and handed it to Dean. 

Dean stared at the paper given to him. It isn’t a business card or anything like that. It was just a piece of paper. Written on it are numbers, a phone number. There’s no name on it either. “What am I going to do with this?”

“That is my number.” James says, as if it was obvious. “Your schedule is currently full for school and work, as mine is with work. Call me when you find time to meet. I will always make time. Now, if you excuse me.”

James stood up. He took his own cup, which is now half-full and nodded at him before leaving. There was no handshake nor a message of goodbye. He just left.

Dean watched James as he left, slightly confused at how the meeting turned out to be. He wasn’t expecting it to turn out the way it did. He looks at the paper at his hand before deciding to save it on his phone. He stared at the contact detail before sighing, placing the name  _ Castiel  _ instead of  _ James.  _ He didn’t know why he did, but it felt right.

He finished his drink and threw it at the nearby exit. He wanted to greet Pamela before he leaves, but he didn’t see her at the counter. This day proved to be the most tiring day Dean ever had, despite the fact that he would be able to rest early. He blew hot air on both his hands, rubbing them both to try and keep them both warm. He drank a cold, coffee drink in a cozy cafe and that wasn’t a great idea, especially if it is a freezing night.

He was just about to round the corner when he felt that he was being followed. Dean has no idea why he would be, since he knew that he looks quite intimidating even at night that being followed wasn’t something he’d ever experience. He stopped walking, waiting for a bit to see if he was really being followed, or he is just being paranoid. He heard approaching footsteps and the next thing he knew, is a pain in the head before everything faded to black.

**_Flashback End_ **

/-/-/-/

Groaning at the headache, Dean tried to get away from his restraints once again. He wonders why he was taken, when he has nothing of value. Besides, he is more worried about the fact that he is supposed to take up a practical exam for a major subject than whatever it is that whoever took him was going to do.

He paused when he heard footsteps. He strained his hearing, turning to the side where he heard it from. He didn’t speak. There was nothing to say.

“Dean Winchester.”

Dean froze. How did they know his name?

“Judging from the pause there, I can tell that’s your name.” A chuckle can be heard before Dean felt a hand on his shoulder. “Care to tell me what you know about Castiel?”

_ Castiel _ . There it is again with that name. “I don’t know what you’re talking about.” He says.

He gets a slap on the face in return.  _ What the hell? _

“Answer honestly and we’ll let you go.” Whoever the person that owns the voice, Dean is going to remember that. He’ll be the first person he’s going to punch once he’s out of the ropes.

“You really think I know? Screw you.” Dean says, almost angrily. All he knew is the name he muttered out of nowhere. “Who the hell are you shits? Did you cover my eyes so I can’t see the cowards that you are?” He asks, taunting them. He has no idea where he is and he knows that this is risking it. Once the blindfolds are off, he can see where they are. It just meant he has a higher chance to escape.

“We’re not stupid. One of us heard you say Castiel. We just want to know who he is and what you know about him.” Another voice says. Dean noted that there are two people in the room with him.

“So, what’s it gonna be,  _ Winchester? _ ”

Dean knows that voice. “Brad? You coward! I knew something was shitty yesterday when you can’t even get at me. You shit!” He growled out. 

He was hit on his right cheek. It was a stronger one that punched the air out of him. They didn’t remove the blindfold. No matter. He will still get out of this. He was doing his best to remove the bound on his wrists. “You can’t make me say shit when I don’t know anything.” He says. And it was the truth. But he knew they won’t buy that.

The sound of motorcycles approaching filled the area that made Dean worry. Are there more of them coming in? What else do they need from him, apart from him apparently knowing Castiel?

He was mistaken when he heard his kidnappers running away in panic. He can hear their frantic footsteps. It would seem that it was not something that they had done in the past. He took the chance to finally break free from his bounds and took his blindfold off.

“Get Dean out of the building, now!” Dean’s eyes are still adjusting from the light but he can hear the screaming from outside. 

Someone holds him by the arm on both sides and he didn’t even fight them off. When he had finally cleared his view, he was outside and he realized that he was held in an abandoned hospital. He looked at the people who had arrived and they all looked unfamiliar… except for one.

“Good day, mi amigo~”

Dean turned around to see Gabriel, a schoolmate. What the hell is he doing here?

This is not helping the headache he is currently nursing.

**_TBC_ **


	4. Chapter 4

**Summary for the Chapter:**

> There are two options that Dean can choose from, according to Gabriel. Which one is he going to choose?

**Notes for the Chapter:**

> I gotta admit, it took longer for me to put this together. I still had school work piled up at the side and I barely have time to translate ideas from my brain to words on a screen. I wanted to scream XD Anyways, thank you for the comments, kudos and the bookmarks. You peeps are my motivation for continuing this, no matter how stress-filled college school works are. Enjoy reading! :D

Dean has no idea what Gabriel was doing there but the distraction made it easy for him to escape. Obviously, he wasn’t alone. Around them, he can see that there are more than 10 people on their own motorcycles. Each of them are wearing different casual clothing, with matching shades. He also noticed that Gabriel is the only one who is not wearing the shades, but it was hanging in front of his shirt. “The hell are you doing here?” he asked. 

It was weird enough to see this group of people gathered at the scene. But it is even weirder when Dean realized that he could see that the sun had just risen from the horizon. 

Gabriel raised an eyebrow at him. “Sure, say that to your one and only savior, Dean-o.” He turned to the people around him, each one of them looking at Dean with mild interest. “Good job, peeps. Get back and tell Cassie Dean-o is saved and there’s nothing to worry okay? I’ll handle it from here.” 

Dean watched as the group left, one person at a time in their motorcycles. Only one remained, and it was Gabriel’s. He rubbed his temples, unable to do anything with the pain. He would need to take something for this later. “What’s this all about? Just... tell me what the hell’s going on, man. I’m about to lose my shit.”

“Ah-ah. No.” Gabriel shook his head. “Actually, we didn’t know it’s gonna escalate to this so soon, kiddo. Cassie mentioned you said his name yesterday out loud. Bad mistake. Aaaaanddd, an oversight on our part.” He drawled out in the end. He gets on his motorcycle, throws a helmet on Dean’s direction and gestures for the other to join behind him. “First, we have to head on back to your place, get ya sorted and let ya go to uni as if nothing happened. After classes, meet me at the cafeteria and we’ll talk.”

It didn’t take long for Dean to respond with a “Fine.” He still had a lot of questions but he decided that even if he is going to ask, Gabriel won’t answer. They had to go if he wanted to get to his classes without being late for his first subject’s pre-quiz. Acting as if being kidnapped was nothing though? He had no idea how he was going to pull that off. He wasn’t shaken- or maybe he was, but he didn’t feel as bad except for his head. It kind of helped that he was angry with Brad and his cowardness.

Gabriel is a pretty chill person. He is within friends of friends and Dean’s upperclassman until he graduated just last year. Dean was able to talk to him before and he knew that he is a well-known player on the campus. Despite that, he is also well-known to be an all-around, good guy who loves to eat anything and everything sweet.

Even if this whole thing is so weird and his sense of normalcy is beginning to crumble down, Dean’s gut says he can trust him, until proven otherwise. He has yet to find out how Gabriel is or not related to Castiel, after all. 

Can anyone blame him if he is being more suspicious and more cautious with _James Novak_ or _Castiel_ , or whatever his name was, more than their very first meeting?

Dean puts the helmet on and gets on, just behind Gabriel and they start to leave. He watched the scenery around him and he found that it was unfamiliar. Just how far away is he from back on their place? “Hey.” He started, unable to hide the worry from his voice. “Sammy’s okay right?”

“Hell ya~” Gabriel replied in a sing-song voice. “Those people who got you last night were amateurs. Like non-professional porn-”

“Sure.” Dean cuts him. “So all those shits were only after me.”

Gabriel nodded his head. “Yep. And we wanna keep it that way if you don’t want dear younger bro to be in danger.”

Just what the hell did Dean sign up to?

-/-/-/-

At school, Dean was able to catch up. He was able to arrive just in time to take his quiz. It wasn't so bad, despite the fact that his headache had probably gotten worse. If Charlie will approach him at lunch, he's gonna have to ask for pain-killers. He can suffer from just about any physical pain. Bring those on and he can take it. Pounding headaches isn't something he'd like to experience for the longest time. It has got to stop now.

Lunch break rolled in without much incident. Dean didn't see Brad and just about any of those people who wanted to give him a piece of their mind in the form of giving him injuries. It was weird and it's making him put his guard up. He didn't want a repeat of what happened last night. Looks like yesterday's Tuesday is the same Tuesday for years, at least to him.

He had his usual, greasy and unhealthy order. The food somehow lifted his mood. He took another bite from his burger when he felt a hand on his shoulder that alerted him of his best friend’s presence.

"What's up bitches- oh! Man you look like crap!" Charlie sat on the chair on Dean's right. She didn’t even wait for his gesture to do so. "Did you even sleep? I heard about your quiz. Did you stay up all night?" Worry can be heard from her voice.

Dean raised a finger to silence her. He took a bite from his burger and sighed. "Yeah, 'bout that, sleep is for the weak." 

"Says who?" Charlie glanced at the long line that has been there since earlier. It was one of the reasons that she had told Dean why she brings her food usually. Although the food is worth it, the line could get people irritated and Charlie doesn't want to be there with those. "Sure man. But look at yourself. Are you sure you're okay?"

Dean can’t blame her for being worried. He had seen himself in the mirror. He looks like crap and he feels like one too. He sighed. "You got anything for a headache?" He asks. He figured that she might have. He did see her with a number of painkillers before. How she had her hands on that many and why, he has no idea.

“Yeah. Hang on.” Charlie rummaged inside her bag and took out a small medicine box. She gave the box to Dean. “Here. You know when to take it.”

“Thanks.” Dean muttered and took the box from her. He placed it on his tray. Then, he slid his fries in between him and Charlie, like he would always do. “Aren’t you going to eat yet?”

Charlie shrugged. She seemed content enough to take some fries from Dean for now. “Mhm? Oh, yeah… I forgot to bring my own food.” She trailed off. For a second, she seemed to be slipping to a daydream before she suddenly jumped, making Dean flinch in surprise. “Before I forgot, have you heard what happened to Brad and his guys?”

Dean was just about to take a bite from his meal. He did take the bite, but he wasn’t chewing yet so Charlie took that as a cue to continue speaking.

"So, word from this morning says that Brad and his guys were kidnapped. There was a ransom and everything. Not sure if the police were involved but woah right? Serves them right."

"They were kidnapped?"

Charlie nods. "Yep, apparently. Or at least rumors say they were. Last night."

The urge to hit someone grew stronger as Dean felt his right eye twitch in irritation. 'No, Brad and his shitty guys weren't kidnapped. _I was!_ ' He wanted to badly say it, but he gulped that down. He knew there is no point in letting his best friend worry further. Besides, he had to keep it low. He still had no idea how deep the rabbit hole goes. “You know what, let them be. Rumors are rumors.” He says instead.

Charlie looked like she was going to say something, but she didn’t. She merely sighed and took some fries from Dean and kept the silence between them.

Dean didn’t say anything at all too. If he were to be completely honest, he has no idea what to say either.

-/-/-/-

Right after lunch, came two more classes. Dean completed both as if time was in fast forward. He had been thinking about what Gabriel had told him this morning. He hasn’t seen his brother yet, but only because Sam had already left when he arrived back at his house to prepare himself for the day.

He did send Sam a voicemail, knowing that he might be worried about where he was the whole night. He did the best thing that he can do, lie. He lied about Pamela needing help in the cafe. It’s not like his brother will check anything work-related, at the moment. Still, it doesn’t erase the fact that he is worried for Sam’s safety.

If he was the target and they caught him off guard last night, what more could happen on his brother right?

Dean found himself walking towards the cafeteria. He had just come from his last class and his mind was slightly, still out of it. So much has happened in a span of two days. It was already a mess and he has no idea what’s going on. If he has some buried memories somewhere, now’s the time for it to get back up and haunt him now so he can deal with it now.

“Dean-o, over here~”

The overall bad feeling came back when Dean heard Gabriel’s voice. Well, the only positive thing that could come from this would be his questions will be answered. The rest all points to the negative. He walks on over to the table where Gabriel is. He is alone and there was nobody else in there other than the two of them. He sat right across him.

“Right. Let’s cut the chase.” Dean started. He made eye contact with his friend. “What the hell’s going on and why the hell are they after me when all I did was say one goddamn word?”

“Pretty eager and straight to the point, I see.” Gabriel says, all traces of his usual jokester’s tone gone. He now meant business and Dean could even see it in his stance, which made him surprised. “Cassie’s a dangerous person.” He started. “Well, not in the sense that you meant dangerous. He’s just given the title ‘cuz he’s our boss. You know, underground orgs and all?” He was whispering. 

Gabriel could practically hear the gears turning inside Dean’s head as he processed the information he had begun dumping to him. He wanted the answers, so he’s gonna give them. He knew that Dean will most likely listen to someone he knows and trusts after all. “He was heir and now he’s the leader in summary. I still can’t say his name ‘cuz listeners all around. It’s like Voldemort ya know? _He who must not be named._ But in general, you can call us a mafia group.”

“Wait- hold on. What?” Dean’s voice was starting to rise. He fought the urge to stand up and pull on the other’s collar. “What the hell has that got to do with me? My life’s normal, Sam’s about to get to college and I’m working my ass off to save up money for both of us. I said the magic word and I got dumped in Alice’s fucking wonderland hole without knowing!?”

“Okay, okay, I get it, you’re angry, frustrated, whatever. That’s cute.” Gabriel stopped him before he started to yell more. That’s not going to end well for them both. He was still undercover as an alumni after all. He cannot let Dean destroy that carefully-crafted image. “This is too much, big guy but suck it up. What do you think we have in our plates for being here longer?” He can’t help but say. “Besides, you’re already connected the moment you decided to help him that night. With or without you knowing, those piece of shits will still be after you. I’m here to answer some questions but I’m here to offer you options. So, are we done throwing tantrums yet?”

Dean did not like where this was going. Two days of non-stop crap and he is about to lose his shit. He didn’t want anything to do with this. All he wanted was to go back in time where he was none the wiser. “Yeah sure.” He reluctantly agreed. He has no choice. He knew that he was in it already. He’s not stupid enough to ask back the normalcy he no longer has. “What’s the options, Gabe?”

“Option numero uno: you get hired to work for Cassie, gain protection for you and your younger bro and reap the benefits. More info on that from the big boss himself.” Gabriel started, right after he showed Dean one finger. Then, he brought the second finger up. “Or you get back to whatever normal life you get and Cassie will cut all ties with you. By all ties it includes: Sam’s sponsor and your tie to him in the past. If there’s peeps comin for ya, we’ll try our best not to let them get near but there’s no promise of protection. What’s it gonna be?

The second option was tempting. He has no idea what was in the past that was trying to get back at him and he didn’t want it, if it is this bad. Now that he knows that they are a mafia, he can’t help but be suspicious of the options, or from the sound of it, it lacks the options for him. Whatever Castiel’s intention was, he knew there was a debt he was trying to pay. Dean didn’t know what it was and he wanted nothing out of it. But he can't choose that option for his brother. Sam had been excited to tell him that he had entered the school he had been aiming for his entire life. His own version of normalcy was gone. Whatever that was left, Dean could tell that his next decision would throw it in the bin for good.

He took a deep breath and with a determined look, he stared right back at Gabriel, finally making his decision.

“I’ll take the first one.”

_**TBC** _


	5. Chapter 5

**Summary for the Chapter:**

> It's the start of Dean's first day and he had to meet his new boss for the terms of the agreement. What could possibly go wrong?

**Notes for the Chapter:**

> Oof- took me a while, my bad. The struggle is real with the paperwork. I can't wait for college to be over ^^" Anyway, this chapter is exactly 2000 words, which is both satisfying and annoying me. I promised I'd cap the word count to 1500 at least and I already failed that XD 
> 
> Enjoy reading~! :D

Today is Thursday. It has been a week since Dean had accepted the option of working for Castiel. Gabriel had been answering any and all questions he had of their boss, unless he said no. Now that he had accepted the first option last week, Gabriel mentioned that he is free to call their boss on any names he can think of or prefers except for Castiel, of course. Dean didn’t like the name James, nor is the nickname most of them use, which was Jimmy. Calling him Cassie seems like a great idea but he figured that he isn’t as close to him as Gabriel was anyway.

So, he decided to call him Cas, for when they talk face to face again, which hasn’t happened yet, ever since he got kidnapped.

Dean had learned a lot from his long-time friend, Gabriel. It helped that he at least knew him and that whatever he had put up in the school, it was all genuine. All that he didn’t expect was that Gabriel is working in a mafia and that is the only secret that he kept close to himself, and Dean is doing the same now too. Anyone is none the wiser.

He and Sam had talked about Dean quitting his work with Pamela because of a new opportunity that arose. His younger brother had expressed his support about his new work and had asked for what it was. He was prepared to answer that he would be working as a personal barista, which was what Gabriel told him to say.

/-/-/-/

**_Flashback_ **

“You serious?” Sam asked. He couldn’t hide the surprise in his voice. Who wouldn’t, when your brother announced he was quitting his job?

Dean nodded his head, face smiling. Gabriel had told him the details on what work he is going to have and more. While he can tell his brother that he is still working as a barista, only as a personal one to some rich guy, as he said earlier, he still couldn’t tell his brother that he is also working under a mafia boss. Secrecy and all that crap. “The guy probably saw my awesome skills. Remember Gabe right? He knows the guy so it’s nothing to worry about.”

Sam had seemed skeptical but he didn’t voice it out even if Dean could somehow sense it. Instead, his brother grinned at him. Dean knows that he is doing this for them and it would seem that Sam looked proud in a way. He knew that Sam was just worried that working as a personal barista might put a strain on Dean’s studies, like his previous works were when the older tried to juggle three part-time jobs while still studying his first year. “You know what, fine, you’re awesome. Don’t overwork yourself, all right?”

“Sam, Sam, Sam- I’m always careful.” Dean grinned back at him. “‘Sides, a level-up yeah? Have you heard of the proposed salary? My student loans will be paid faster than when I was working at the cafe, no problemo. Soooo-” he drawled and opened the fridge to take two bottles of alcoholic beverages. “Celebration’s in order, Sam! Drink!”

**_Flashback end_ **

/-/-/-/

They did drink that night to celebrate, which was nice because it has been so long since Dean drank anything with alcohol in it, especially since he had to do school and work sober. He had little to no time to actually sit around and do nothing. He was so used to it that he, even sitting down, makes him feel like he has to be doing something.

Which brings Dean to his current predicament. Today is his first day for his new job. He had quitted from Cafe Bonheur five days ago and Pamela had taken it well. He still hangs around to help for those days, even if he didn’t get paid for that anyway. He owed it to Pamela that he and Sam were still in school and studying as Dean worked so he knew that he just had to. 

Right after his classes, Gabriel came to get him to ride the motorcycle with him back to Castiel's place, a favor granted for a week at most. Gabriel told him that his schedule was from 6pm-12am, which was his usual working shift and that he may or may not have the big boss come to discuss with him the finality of the option that Dean had agreed to. It flared up the nervousness but he had that hidden with a frown.

They arrived at Castiel’s place not too long ago. If Dean would be asked, calling it Castiel’s  _ place _ is an understatement, of course. They arrived at a mansion that he thought would only be seen in movies. It was only a few miles from the university but it was far enough to be considered, somewhat, secluded. Gabriel led him from the service entrance, passed the huge front lined up with trees and greenery that were all well-kept, which made it look like the inside a luxurious garden, before they finally reached the front doors. Once they stopped there, Dean got down and handed the helmet back to Gabriel.

“Where am I going after this?” Dean asked, looking around him. He has an impeccable sense of direction, so he won’t get lost. But that would be the case if he knew where’s where.

Gabriel raised an eyebrow at him. “Ask around, Dean-o. Get in and look for a person named Meg, she’ll help. If Cassie comes around, say heya for me. See ya later and good luck!” He waved at him a goodbye before gesturing for him to come in. Then, he left.

Dean watched Gabriel leave. He turned to the door, debating for a second if he should knock or not. When he saw the intercom at the side, he realized he had to press the doorbell of sorts. He pressed for a bit and waited.

“Yes?” Someone answers him from the inside. She sounded as if she was talking to a child, but maybe that’s just Dean.

“Uh yeah. It’s my first day. I’m Dean Winchester.”

The sound of a click and the door opened. Dean made eye contact with a shorter female wearing an all black outfit. She is wearing a leather coat over a black shirt, ripped jeans and three-inched boots. She gave him a smile and offered her hand. “It’s nice to meet Clarence’s new boy toy. My name’s Meg. Welcome, Dean Winchester.”

_ Boy toy?  _ Dean shook her hand and looked around him. “Sure, do I get to talk to Cas?” He asked, straight to the point. He had to know how things would go for his new work.

Meg smirks at him, then gestures for him to follow her. “Straight-forward.  _ Mhmm-  _ Follow me.” She hummed and started to walk. She didn’t even turn to Dean to see if he was following her at all.

Dean followed her anyway, looking around him as he walked. The first thing that he noticed are two grand staircases on either side right in front of him. The floor has peach tiles, and at the very center of the room, in between and just a few distance away from both stairs, is a circular, red carpet. It seemed out of place at first, but the black lining of the stairs’ handles and the brown doors from the cardinal directions made it work. 

It was luxurious, and also minimalistic on its own too. Dean was no interior designer, but seeing the place uncrowded felt pleasing. They took the stairs at the right and he had just noticed that they were also tiled, like the floor, but they were lined with a carpet with a dark shade of green. There is also a chandelier hanging directly above the red carpet below. 

Meg opened the first door on their right when they got to the next floor. Then, she turned to Dean. “Honestly, even I have no idea if he’s gonna come around and meet you, Dean.” She was smiling at him. She giggled when all she saw was a frown and impatience on the new employee. “ _ Ah,  _ you’re interesting.”

“Can you just send me to my workstation or wherever I have to be so I can get started?” Dean is tired with all these people thinking that he is  _ interesting  _ or that he knows something about this  _ Castiel.  _ He won’t ask anyone to forgive him for being rude, he never asked for this anyway, even if he had already agreed.

“Tut tut, cowboy. Didn’t know about patience, hm?” Meg shook her head slightly in amusement before finally walking down the hallway beyond the door she just opened.

The very first door that they saw is at their right, but also a good distance away from the door too. For what reason, Dean didn’t know but it wasn’t where Meg was leading him to. The first door on the left was only two feet away from the door they just passed by. It seemed that the pattern of the doors here was made so that the rooms will make it possible for a better emergency response, in case. It was still a large hallway though and he wasn’t even given the chance to wander because Meg was knocking on the second door they passed by.

“Clarence, it’s Meg.” She announced, her hand now on the handle. “Your new recruit is here.” She opens the door.

Dean was greeted by the smell of books. It was then that he realized that he is either in a study, or a library, or both. He wasn’t in just yet, but he can see the bookcases lined up at the left side. His focus wasn’t there though, it was on the only man in the room. The blue-eyed person that he had helped on that one Monday that also happened to throw his life into a spiral of mess.

He made eye contact with him and there was silence hanging in the air. Blue met green head on, neither one making a sound at all.

“Ah, the classic  _ eye-fucking. _ ” Meg groans, rolling her eyes. Dean cleared his throat when he heard that.Their staring broke. “I’ll be by the bar when you need me, Clarence. Enjoy the reunion~”

When Meg walked away, Dean finally took a step in the room and closed the door. “How do we do the arrangement thing?.”

He heard a pause before a small sigh. “Sit down, Dean.”

Dean did as he was told. There were small sofas that were facing each other, right in front of the desk of his boss. Now that they are the only ones in the room, it was time for him to give a piece of his mind. “Whatever our history is. I don’t want jack shit about it. Can you cut that out?”

“Understandable. That’ll be part of the contract. Anything else?”

There was tension in the room, so thick anyone could cut it with a knife. It didn’t faze Dean though, as he nodded his head. He looked at his hands for a brief moment. “I accepted the option because I have no choice. Gabe said it’ll be temporary shit but I don’t have anything to add other than what he talked about. So, just tell me what I have to do and I don’t care about the rest, Cas.”

The sound of breaking glass made Dean look sharply up. He caught sight of Castiel looking at him in surprise. He seemed to have frozen for a bit before his expression hardened, stone cold. Dean saw the small pieces of one of the glass figurines on the desk. “If you don’t give  _ jack shit  _ about our history. Do not call me that. Leave. Now.” Castiel was glaring at him as he pointed at the door.

Dean stood up and left the room. Right after he closed the door, he just stood there, staring at it and wondering what the hell just happened?

**_TBC_ **

  
  


**Notes for the Chapter:**

> Oh and I'm planning on making another SPN fanfic again XD
> 
> Do you peeps have any suggestions? Because I wanna try a different genre. And if there isn't I might try non-traditional A/B/O (just because I haven't tried writing a piece with that genre ^^") as a challenge.


	6. Chapter 6

**Summary for the Chapter:**

> Memories-turned-nightmares, those were the source of Castiel's guilt. Recurring dreams of the past was something he used to punish himself to this day. Without Dean even knowing who he was, Castiel knew that the past on Dean's perspective was worse.

**Notes for the Chapter:**

> Henwo! This time, we have Castiel's POV! I didn't plan for this to happen, but it did anyway. This chapter practically wrote itself and I am the medium XD Honestly, I didn't even try to cap my word count and this turned out to be more than 3000. Thank you for you peeps who are still reading and commenting here. I can't believe that you peeps love this as much as I love writing this. 
> 
> Oh, and I'm editing tags, adding or removing them as I go. So characters may be added.
> 
> Anyways, enjoy reading!! :D

_ “Dean! You can’t!” He hears himself say, voice echoing around him. _

_ A sudden breeze of cold air passed them, making Castiel shiver. The clothing that he is wearing isn’t appropriate for the cold night, neither is it enough to keep the 7-year-old warm. He was wearing a fur jacket or at least it would be if the fluff on it wasn’t slightly destroyed and he had been wearing a scarf and a hat at one point. Now, all he has is his jacket, the crochet hat gone from all the running that they did or maybe even before that. _

_ He is currently hugging an arm, which belongs to a kid almost of the same age as he is. Dean was younger by a few months, but he was taller and bigger than Castiel was. Castiel was scared, he didn’t know where they both were but he knew that he didn’t want to leave Dean here, like the younger had insisted. It was a large forest and even if he would join his father around, he wasn’t familiar with the place. _

_ “Come on, Cas.” Dean’s voice was small and Castiel can tell that he is trembling from the cold like he is. He had given his friend the scarf he had on. But it wasn’t enough because he is only wearing a shirt. It was cold and it felt like it would be snowing at one point. “Your dad’s gonna be worried. You have to go. It’s okay, just follow the trail.” _

_ Castiel shook his head, refusing to let go of Dean’s arm. “No! We promised right? We planned that so we could escape, we could run!” _

_ Dean pried Castiel’s hands off of him. He held the older’s face with both of his freezing hands. He forced him to make eye contact. “Cas, I’ll be fine, yeah? Besides, I have this scarf I have to return to you.” He giggles, looking at the scarf around his neck for a brief moment. “I won’t be long okay? Just run and hide like we promised. Count to 10 to yourself once you know you’re safe and I’ll come.” _

_ Reluctantly, Castiel nodded his head. “Okay. You’ll come, right, Dean?” _

_ Dean smiled at him, trying to hide his fear but Castiel can see it in his eyes. “I promise.” _

_ Castiel nodded his head and held his hand. The small pinky promise caught Dean off guard but he indulged him. Soon, they can hear their pursuers going closer. Only one look from Dean made him turn around to follow the trail that his friend had told him to. His eyes were blurry with tears but he continued on. They promised and they survived this long. _

_ Dean would surely follow right? _

_ Unable to stop the tears from falling, Castiel continued to run but he was wiping his eyes as he did so. The cold air was making his entire body numb but he kept moving forward, not even once did he look back. When he saw the big tree that Dean mentioned, he hid at the other side of it, sliding to the ground and hugging his knees close to his chest. He closed his eyes and began to count down from 10. _

_ But when he finished, the echo of a gunshot was heard. He stood up, worry filling his little frame. It came from where he was from. Castiel was just about to come back when he felt a hand on his shoulder. Turning, he saw his father, wrapping a jacket around him. _

_ “Papa...” Castiel was full-on crying now, half with relief and half with worry. “Dean… Dean is still there…” _

_ “Just sleep, Castiel.” He heard his father say. He carried his son and made his head lay on his shoulder. “We’ll do our best to find him. Don’t worry.” _

_ Days turn to weeks, and weeks to months. Castiel never heard from Dean again. _

_ His father had promised to look for his friend but Castiel stopped them, once one of his father’s men found the bloody scarf that he had lent Dean. He took the scarf from them, and entered his room, where he wept in regret. _

-/-/-/-/-

Castiel opened his eyes, turning to the side to check at the time. It was a little over 4am. He blinked, sniffed, and wiped the tears from his eyes. He had been holding onto the memories of the past that it became a nightmare that plagued him with grief, both in dreamland and in his waking hours. It was exhausting to have the recurring memories come to him every night, but he felt like he needed that to punish himself for giving up in the past.

An hour and a half of sleep was enough for him. He is lucky if he actually had three on any night. His dream was melancholic today it seemed. It was full of guilt but he prefers this, unlike the many others where his mind would actually make up scenarios where he had actually seen Dean dead. Nothing was pleasant but he thinks that his dream went back to the guilt because he now knows that Dean is alive and well, but has no memory of him, it seems.

He stood up and made his way to the bathroom, cleaning himself up before going down to grab himself breakfast. It was still way too early, but the maids knew how much of an early riser Castiel is. When he went downstairs and to the dining room, a meal was already prepared there for him, another plate was on the right which meant that someone was also awake by now.

Castiel sat at the head chair. It was quiet, other than the sound of footsteps of the maids that were in the morning shift. He could hear them talk in the kitchen, but not enough to hear actual conversation.

“Ever the morning riser, Cassie. Can’t sleep?”

Castiel didn’t need to turn around to know that it was Gabriel. “And you woke up early today. That’s new.”

“Naww, bro. You make it sound like I wake up  _ late. _ ” Gabriel pulled the chair on Castiel’s right. He served himself, then turned to his younger brother. “Ya know he’s alive for a week, Cassie, he’s  _ fine. _ ”

Sometimes, Castiel hates it when Gabriel knows just what to say. Right now though, it was the closest to reassurance that he can get in this family. Ever since he was taken and he gave up on looking for Dean after only finding his scarf, every single one of the family started to get stone cold. He had forgotten what warmth felt like.

Then again, he wouldn’t have been able to keep the whole family in line if he was weak. He kept up his appearances, did as he was supposed to do, kept his emotions locked up and stayed professional. Without doing those, he won’t be a part of the family. Most definitely, he won’t be the head in charge now if it weren’t for his efforts.

“Of course, he’s  _ fine. _ ” Castiel says, not even giving as much a glance over at Gabriel’s direction. “I never stopped looking for his whereabouts when I stepped in position. But before Monday we never found a single trace of him. The moment my guard was down, he just seemed that he appeared out of nowhere.”

Gabriel shook his head at him. “Nuh-uh. For all Dean-o’s aware,  _ you’re  _ the one who ‘appeared of nowhere’. I told ya we have to wait.” He sighs. “Making contact after the incident was bad enough, and now he knows your actual name.” The older Novak took a spoonful of his meal. “And after that meeting, he got kidnapped.  _ Yikes _ , Cassie, see?” 

Castiel didn’t reply to that, merely stared at his plate. He knew how much of a risk it is to establish contact with Dean. It was dangerous, for both of them. It was reckless and it wasn’t something he knew he would’ve done if he was in the right mind. The guilt ate at him and he was ashamed to admit that he gave up his search, that he didn’t wait when he promised he would.

“The risk was high but I can’t blame ya.” Gabriel continued. “Besides, they’re both graduating soon and transferring states. We’ll be gone, they’ll be gone and Milton stays-”

“Sure.” Castiel replied. He didn’t like where this was going. It is leaving a sour taste in his mouth. He is just halfway through his food but he found out that he had lost his appetite. “I’ll be in the study the whole day. I have a business meeting. Meg’s returning this afternoon too. Good luck with the mission, Gabriel.” With that, he stood up, left his unfinished meal there with his older brother and went right back upstairs to his room. He needs to mentally prepare himself for all the questions Dean must have in mind.

-/-/-/-/-

In a business like this, everything is a family matter. Granted, there are some of the members in the Novak mafia that weren't really related to them, but they were few in number. Still, they were still greater in number than those who merely pulled off members that weren’t kin. In the family, they can rely on each other. That was how they stayed as the strongest underground.

Partnerships are rare, but when families establish agreements, both parties become even more powerful. So, Castiel had to put up with the business meeting front that he’ll have later. He had to be ready to offer something that is of equal value to his family’s demand. Unless, the Lafitte’s have their own offers themselves. Either way, their partnership, if ever, will benefit both families.

True to his word, Castiel was in his study. He had just eaten his lunch before he went there. Reading a few books to pass the time was one of his hobbies, next to archery practice. It took his mind off things and it kept his mind sharper at the same time.

It was past five in the afternoon when he finished his book. He had asked Megan, one of his maids, for coffee and to remind him when Meg finally arrives. He was checking his phone for the emails he had been receiving the whole day, sifting those that he deemed important enough to reply now from those he can prolong a reply until the next day.

The knock on his door was a welcome sound. He wanted to drink his usual, late afternoon coffee. The thought of it was pleasant. He needed it to get by through the meeting later, after all. Only, it wasn’t Megan.

“Clarence, it’s Meg.” Castiel hums to himself. He had been hoping for a little energizer first before she arrived. Looks like he is wrong to assume that he could. “Your new recruit is here.”

Those were the words that made him freeze for a second. He was able to gather his composure, his usual poker face on, before the door opens to reveal both Meg and… Dean.

Castiel would be lying if he said that he wasn’t nervous. But he is also intrigued. Sure, Dean didn’t know what he is capable of and just how much of a danger he is, yet, he is staring at him head on. He tilted his head slightly to the side, curious and daring Dean to say something first.

Of course, Meg has to ruin it. “Ah, the classic  _ eye-fucking. _ ” The groan made Castiel narrow his gaze at her direction. “I’ll be by the bar when you need me, Clarence. Enjoy the reunion~”

Classic Meg who always says what she has in mind. Meg and Gabriel are more similar than they think they are. They usually fight after all.

Castiel didn’t answer, merely glared at her as she left. He’s now alone in the room with Dean. He admires how Dean stands up for himself. He was just like the child that Castiel remembered, strong, defiant and would do anything for his brother.

He knew that it was too soon, and since Dean had mentioned not wanting anything from their past, Castiel is ready for that. He had made himself aware that this might be one of what Dean would like and he wasn’t wrong. Besides, there was nothing else that his friend had remembered from the past, other than his name.

The months-long they spent together then, the nickname Dean gave him and their escape attempt… Those were things of the past. Castiel still wanted to help him with anything. He owed him his life and he still feels guilty over leaving him and giving up on him. But if there was nothing he could remember, it was nice to start anew- back to the very start.

“I accepted the option because I have no choice. Gabe said it’ll be temporary shit but I don’t have anything to add other than what he talked about.” Of course, it was temporary, but Castiel didn’t say it out loud. He knew that it would be weird to send Dean money without him suspecting so he had arranged him to work for him a bit. That way, he didn’t have to keep working for years before he paid off the student loan he had taken. 

“So, just tell me what I have to do and I don’t care about the rest, Cas.”

He froze. The glass figurine in his hand crashed on the sudden pressure that he gave it. Some pieces fell on the desk, others on the floor. The sudden burst of emotion was overwhelming him. It took every inch of his being not to stand up and hug Dean for remembering. But he saw the expression on Dean’s face. It wasn’t that he remembered, it was that he just thought it  _ right. _ That was the trigger. He wasn’t able to stop himself from making Dean leave.

The moment he is left alone in the room, Castiel closes his eyes tight, trying to calm the raging emotions within him. He had to reign them all in, just like he always does.

The knock on the door was back. This time, it wasn’t a welcoming sound. He just wanted to be left to his own devices at the moment. He didn’t like to face anyone else until before his meeting is finished, which is still a few hours from now.

Before he can reply though, he heard Dean’s voice from the other side. “So, uh. I got you coffee.” The door opened after that and Dean entered, pushing a small cart along with him. “Also, figured you’re bleeding after the glass so I have the first aid here. Fucking knew it.”

Castiel looked at his right hand. He looked at Dean in slight surprise. He had gotten used to ignoring injuries that there are times that he forgets he is in pain. Just like last monday… just like today. “Dean, I told you to leave.”

“Yeah, you did.” Dean nodded his head. He grinned at him and shrugged. “And I did. But I’m back. Lemme see your hand.”

Speechless for a bit, Castiel showed him his hand. Dean approached him and took it, clicking his tongue and took the kit from the cart and placed it on the table. “It’s a shallow wound. It will heal in time.” He says, looking at how careful Dean was in removing the smaller shards that were still on his skin.

Dean hums his response. “True, but it’ll hurt like a sonovabitch when ignored. Besides, infections are not fun.” Once he was sure there were no more shards, he began to clean it.

A sharp hiss came from Castiel, the pain finally registering. “You don’t have to do this.” He says, trying to get his mind away from how much the wound hurts. “It is not part of the agreement that we have yet to talk about. I think Gabriel told you what you will be doing.”

“He did.” Dean nodded his head. He took the gauge bandages and the medical tape and started to work on dressing the wound. “The coffee’s right there. ‘Saw Megan by the stairs, asked her where the kitchen was. Your maid forgot to prepare your coffee so I prepared that.”

Castiel was watching Dean as he dressed his wounds gently and expertly. Even if Dean couldn’t remember it, Castiel noticed that his friend never really changed even after all those years. The guilt started to eat at him again. Whatever happened then that made him repress his memories of him like that, Castiel could only guess it was that  _ bad. _

“I apologize for lashing out.” He says, finally looking up to meet Dean. He was slightly surprised to see him staring back at him too. 

“Yeah, well, I called you by the nickname I thought of outta nowhere so it’s my fault.” Dean smiles at him and lets go of his hand. “Careful with your that. You might reopen those if you move too much.”

But it wasn’t Dean’s fault, Castiely knew it was his. He didn’t say anything though, merely looked at his bandaged hand. Nobody in his family has ever done that to him. Dean was careful the whole time and he can tell that it has nothing to do with his status, because he can tell that Dean could stand his ground around him head on. It was weird and it made him confused. “Right… we were talking about the arrangement...”

Dean hums, taking the cup of coffee and placing it on Castiel’s desk. “Yeah we were. Do you mind if I call you by that name or do you want a different-”

“That’s fine.” Castiel answered, a little too quickly despite himself. He cleared his throat. “I was caught off guard earlier. But I’m fine with it.”

Without Dean’s memories, maybe Castiel can finally throw away the guilt eating at him for years. For now though, they had business to do. The arrangement would be beneficial for Dean as it is for him. He would get rid of the final emotion plaguing him. Maybe, after this temporary help, he won’t have to punish himself with those memories. Perhaps, finally, this is the first step for him to focus nowhere else but the family.

Family was everything in his line of business after all. 

**_TBC_ **

**Author's Note:**

> Oh yeah, I do take ff requests. But don't be upset if I didn't pick your request. I will still handpick which prompts I'll do so yeee-


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